Alkylation of aldehydes with trialkylboranes in water

被引:16
作者
Hirano, Koji [1 ]
Yorimitsu, Hideki [1 ]
Shima, Koichiro [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
关键词
aldehydes; alkylation; cyclodextrin; nickel; trialkylboranes; water;
D O I
10.1002/adsc.200606136
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Water enables the alkylation of aldehydes with trialkylboranes under nickel catalysis without the addition of a base. Trialkylboranes prepared from borane-dimethyl sulfide and terminal olefins via hydroboration as well as commercially available trialkylboranes could be employed for the reaction. The reaction would proceed via eta(2)-coordinated nickel complexes with aldehydes as the key intermediates.
引用
收藏
页码:1543 / 1546
页数:4
相关论文
共 31 条
[1]   Cleavage of water-insoluble alkylallylcarbonates catalysed by a palladium/TPPTS/cyclodextrin system: effect of phosphine/cyclodextrin interactions on the reaction rate [J].
Binkowski, U ;
Cabou, J ;
Bricout, H ;
Hapiot, F ;
Monflier, E .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 215 (1-2) :23-32
[2]   Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes [J].
Biswas, K ;
Prieto, O ;
Goldsmith, PJ ;
Woodward, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2232-2234
[3]   EFFECT OF POLAR-SOLVENTS ON THE RATES OF CLAISEN REARRANGEMENTS - ASSESSMENT OF IONIC CHARACTER [J].
BRANDES, E ;
GRIECO, PA ;
GAJEWSKI, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :515-516
[4]   A CONCISE CHEMICAL SYNTHESIS OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN) [J].
CHAN, TH ;
LI, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) :747-748
[5]   SYNTHESIS AND CLAISEN REARRANGEMENT OF ALKOXYALLYL ENOL ETHERS - EVIDENCE FOR A DIPOLAR TRANSITION-STATE [J].
COATES, RM ;
ROGERS, BD ;
HOBBS, SJ ;
PECK, DR ;
CURRAN, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1160-1170
[6]   THE CONFORMATIONAL EQUILIBRIUM OF CHORISMATE IN SOLUTION - IMPLICATIONS FOR THE MECHANISM OF THE NONENZYMATIC AND THE ENZYME-CATALYZED REARRANGEMENT OF CHORISMATE TO PREPHENATE [J].
COPLEY, SD ;
KNOWLES, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) :5008-5013
[7]   SELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA [J].
EINHORN, C ;
LUCHE, JL .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) :177-183
[8]  
Fürstner A, 2001, ADV SYNTH CATAL, V343, P343
[9]   ON THE MECHANISM OF REARRANGEMENT OF CHORISMIC ACID AND RELATED-COMPOUNDS [J].
GAJEWSKI, JJ ;
JURAYJ, J ;
KIMBROUGH, DR ;
GANDE, ME ;
GANEM, B ;
CARPENTER, BK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1170-1186
[10]  
Grieco P.A., 1998, Organic synthesis in water